Triethylamine → Benzoic acid N'-(3,3-diphenyl-propionyl)-N'-isopropyl-hydrazide

HRID 1724150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724150
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]([NH:21][NH:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:20])[CH3:19].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[C:12]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C:9]([N:21]([CH:18]([CH3:20])[CH3:19])[NH:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 188691-Benzoyl-2-isopropylhydrazineHCID 64798Diphenylpropionic acidHCID 757711-Hydroxybenzotriazole

Produkt 1

HCID 57560100Benzoic acid N'-(3,3-diphenyl-propionyl)-N'-isopropyl-hydrazideAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3,3-diphenylpropionic acid (127 mg, 0.56 mmoles) and benzoic acid N′-isopropyl-hydrazide (100 mg, 0.56 mmoles) in DMF (5 mL) was treated with triethylamine (0.23 mL, 1.68 mmol), HOBT (91 mg, 0.67 mmoles) and EDCI (129 mg, 0.67 mmol) at room temperature for 18 h. The reaction mixture was partitioned between water and dichloromethane. The organic layer was washed with water, dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient to afford the product as a solid (59 mg, 27%). LC-MS m/e 387.26 (M+H+)

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient

Quellen und Nachweise

ORD-Eintrag
ord-512fbd1471484c94ae6594685b623ea6
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485752B2

Notizen zur Reaktion

Wird geladen…